Water → N-(5-Bromothiazol-2-yl)-N-methylacetamide

HRID 910291Notes

Reaction equation

HRID 910291 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[Br:9][C:10]1[S:14][C:13]([NH:15][C:16](=[O:18])[CH3:17])=[N:12][CH:11]=1.O>CC(C)=O>[Br:9][C:10]1[S:14][C:13]([N:15]([CH3:1])[C:16](=[O:18])[CH3:17])=[N:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3502602-Acetamido-5-bromo-1,3-thiazole

Product 1

HCID 67147803N-(5-Bromothiazol-2-yl)-N-methylacetamideYield 36.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.9 g (14 mmol) of potassium carbonate and 3.94 ml (63.3 mmol) of methyl iodide are added to a solution of 2.8 g (12.7 mmol) of N-(5-bromothiazol-2-yl)acetamide in 50 ml of acetone. The reaction medium is refluxed for 3 hours. After addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 1.1 g (36%) of N-(5-Bromothiazol-2-yl)-N-methylacetamide are obtained.

Workup

  1. temperatureThe reaction medium is refluxed for 3 hours
  2. extractionthe reaction medium is extracted with ethyl acetate
  3. washThe organic phase is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-9c25c526976d4121a3b6d76d1c0850d8
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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